O-Toluidine
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Basic Info
Common Name | O-Toluidine(F05289) |
2D Structure | |
Description | The chemical properties of the toluidines are quite similar to those of aniline and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic. None of the toluidines is very soluble in pure water, but will become soluble if the aqueous solution is acidic due to formation of ammonium salts, as usual for organic amines. At room temperature and pressure, ortho- and meta-toluidines are viscous liquids, but para-toluidine is a flaky solid. This can be explained by the fact that the p-toluidine molecules are more symmetrical and fit into a crystalline structure more easily. p-Toluidine can be obtained from reduction of p-nitrotoluene. p-Toluidine reacts with formaldehyde to form Troger's base. |
FRCD ID | F05289 |
CAS Number | 95-53-4 |
PubChem CID | 7242 |
Formula | C7H9N |
IUPAC Name | 2-methylaniline |
InChI Key | RNVCVTLRINQCPJ-UHFFFAOYSA-N |
InChI | InChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3 |
Canonical SMILES | CC1=CC=CC=C1N |
Isomeric SMILES | CC1=CC=CC=C1N |
Wikipedia | O-Toluidine |
Synonyms | 2-AMINOTOLUENE o-Toluidine 2-Methylaniline 95-53-4 2-Toluidine o-Tolylamine 2-Methylbenzenamine ortho-toluidine o-Methylaniline Benzenamine, 2-methyl- |
Classifies | Pollutant |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Toluenes |
Intermediate Tree Nodes | Not available |
Direct Parent | Aminotoluenes |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
Substituents | Aminotoluene - Aniline or substituted anilines - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic homomonocyclic compound |
Description | This compound belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 107.156 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 1 |
Rotatable Bond Count | 0 |
Complexity | 70.8 |
Monoisotopic Mass | 107.073 |
Exact Mass | 107.073 |
XLogP | 1.3 |
Formal Charge | 0 |
Heavy Atom Count | 8 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9625 |
Human Intestinal Absorption | HIA+ | 0.9906 |
Caco-2 Permeability | Caco2+ | 0.8599 |
P-glycoprotein Substrate | Non-substrate | 0.8504 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9541 |
Non-inhibitor | 0.9869 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8785 |
Distribution | ||
Subcellular localization | Lysosome | 0.7562 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7992 |
CYP450 2D6 Substrate | Non-substrate | 0.8614 |
CYP450 3A4 Substrate | Non-substrate | 0.7676 |
CYP450 1A2 Inhibitor | Inhibitor | 0.6284 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8051 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9406 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.7568 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9445 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6737 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9514 |
Non-inhibitor | 0.9344 | |
AMES Toxicity | AMES toxic | 0.8875 |
Carcinogens | Non-carcinogens | 0.5479 |
Fish Toxicity | High FHMT | 0.6676 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.8900 |
Honey Bee Toxicity | Low HBT | 0.7032 |
Biodegradation | Not ready biodegradable | 0.7073 |
Acute Oral Toxicity | III | 0.7892 |
Carcinogenicity (Three-class) | Non-required | 0.7094 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.9127 | LogS |
Caco-2 Permeability | 1.7144 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.1987 | LD50, mol/kg |
Fish Toxicity | 2.0744 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.2570 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Determination of primary aromatic amines in cold water extract of coloured paper napkin samples by liquid chromatography-tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 Jun | 27146949 |
Modulation of antioxidant defence system by dietary fat in rats intoxicated with o-toluidine. | Hum Exp Toxicol | 2002 Dec | 12540036 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]